Diverse continuous photooxygenation reactions of (+) and (−)-α-pinenes to the corresponding pinocarvones or trans -pinocarveols

In this study, the continuous photooxygenation reactions of (+) and (−)-α-pinenes are described. The corresponding hydroperoxides were continuously processed under mild conditions using Ac 2 O and a base to yield (−) or (+) pinocarvones in up to 79–83% yield and a 12–13 g-scale. Alternatively, the h...

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Bibliographic Details
Published in:Reaction chemistry & engineering 2023-03, Vol.8 (4), p.790-797
Main Authors: Rosa, Gabriel H. S., Santos, Thiago I. S., Brocksom, Timothy J., de Oliveira, Kleber T.
Format: Article
Language:English
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Summary:In this study, the continuous photooxygenation reactions of (+) and (−)-α-pinenes are described. The corresponding hydroperoxides were continuously processed under mild conditions using Ac 2 O and a base to yield (−) or (+) pinocarvones in up to 79–83% yield and a 12–13 g-scale. Alternatively, the hydroperoxides were reduced with Ph 3 P giving pinocarveols in up to 61% yield and a 10.8 g-scale. Our protocols proved to be efficient, easily scaled up and safe while processing unstable hydroperoxides in the g-scale (24 h experiments). Additionally, we describe a variable we named efficiency ( E ) which was useful to rationalize the best reaction conditions for the best yield, also including the productivity and non-processed starting materials.
ISSN:2058-9883
2058-9883
DOI:10.1039/D2RE00385F